


down a few pegs

by scandalous



Series: Season of Kink 2019 [21]
Category: The Good Place (TV)
Genre: Anal Fingering, Bottom!Chidi, Dorks in Love, Established Relationship, F/M, First Time Bottoming, Pegging, Strap-Ons, Top!Eleanor, set during one of the reboots
Language: English
Status: Completed
Published: 2019-09-13
Updated: 2019-09-13
Packaged: 2020-10-17 20:42:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,382
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20627243
Author URL: https://archiveofourown.org/users/scandalous/pseuds/scandalous
Summary: Eleanor finds out Chidi hasn't ever gotten pegged. And, well, that requires some fixing.





	down a few pegs

**Author's Note:**

> for seasonofkink with the square 'first time'.
> 
> enjoy!

“You’ve never gotten pegged?” Eleanor gasps out, eyes wide as she turns to Chidi.

He looks away, smiling a tad nervously. “It’s just— no girl I was ever with was interested on that and, yeah. It’s a very political act, though, I’ve got to say—”

She can’t help but laugh, pulling him into a quick kiss. “You can talk to me about the gender politics of a man taking a strap-on after I’ve done that to you.”

“Okay,” he breathes, looking up at her with that loving smile that makes her weak at the knees. “How do we get the lube and the strap-on?”

Eleanor rolls her eyes. “Oh, c’mon, we’re in the Good Place. We can get anything we want!” She gets up and turns around. “Janet?”

Bing! “Eleanor.”

“Hey,” she says. “I’d like some lube— like, sex lube— and, well, a strap-on dildo, if that wouldn’t be much issue.”

Soon enough, Janet summons up the objects she requested. The lube is in a nicely-sized container, perhaps for quite a few uses, and the dildo is maybe six, seven inches. 

“Is that too big?” she asks, turning around and showing it off to Chidi.

He shrugs. “I don’t know, really. Again, I’ve never… done this before, so I wouldn’t know. Isn’t it typical dick size, though?”

“A little bigger than typical dick size. With enough lube we should be fine, though, I think.”

Janet perks up, “In the Good Place, there is no tearing and no sexually transmitted diseases.”

There’s silence for a couple seconds before Chidi says, “Yes. Thank you, Janet. You can go now.”

Bing!

Eleanor sighs in relief. “Okay, she’s gone, great! Let’s get you ready and all of that. You heard her, there’s nothin’ that can hurt us in that matter in here. But I’ll still be careful, because I’m used to it.”

“What a way to say you had a lot of sex back on Earth,” he says as he’s dragged to their bedroom, smiling as he keeps kissing her, letting her start taking off his clothes one by one. “You’re such a bragger.”

“Oh, with those arms it’s not like you weren’t getting any,” she teases.

Chidi laughs a little at that, running his thumb over the back of her hand as he leans down to kiss her. “Everyone hates philosophy professors. Even the hot ones.”

She rolls her eyes. “I don’t hate you, though. Now, uh… should we go typical doggy-style or?”

He bites his lip, looks around like there’s something very interesting on the walls. “Maybe we should keep missionary.”

“Why are you so vanilla?” she whines out dramatically as she grabs a pillow, putting it by the end of the bed. “C’mon, get your ass on there. On the pillow, I mean. You know.”

“I know,” he replies with a little laugh as he settles in, his ass raised ever a little, letting her easy access to his entrance. His cock is already twitching into hardness, curious at this new experience that makes every hair on the back of his head raise. He’s always liked new experiences.

She leans in to kiss him before reaching down, squatting a little to get a better position to start fingering him. She squirts some lube onto her fingers, biting her lip as she focuses.

“Tell me if anything feels off, okay? It’s a first time thing, and it’ll feel a little weird, but if I do this right, everything should be fine.”

Chidi nods a little, spreading his legs farther apart. “Yeah,” he nods. 

She leans in and kisses the inside of his thigh, her clean hand running up his leg as she smiles. “Okay;” she says quietly as she prods at his hole with her index finger, her hand leaning up to his cock, giving it a few nice strokes to relax him before she pushes it in.

“Oh,” he gasps out, tilting his head back. “That’s… weird.”

“It is,” she agrees, laughing a little. “Is it okay, though?”

He nods, his cock half-hard on her hand. “Yeah, keep going.”

She obliges, pushing her finger deeper in before she starts to prod at his entrance with her middle finger before pushing it in gently, watching him stretch out around her. “You’re doing great, Chidi,” she says.

“I’m enjoying it,” he says. “It’s… weird, but it’s pretty good. Can’t wait until I get the actual thing inside me.”

She laughs, pressing a kiss to his thigh once again. “I didn’t know you were such a bottom, Chidi.”

He laughs too. “I didn’t know either!”

She starts scissoring her fingers carefully, looking up at Chidi from time to time to smile at him as she stretches him out. It’s a pleasing experience, alright, having the privilege of doing this to Chidi when he hasn’t ever done it before. It’s almost like taking his virginity in a way that makes her hot and bothered all over.

“Up for another finger?” she asks carefully. “The strap-on isn’t too thick, but just to make sure.”

Chidi props himself up with his elbows and nods. “Yeah, I think that’d be good.”

She pushes a third finger into him and pushes them in and out, slowly, making sure to not overwhelm him. “Let me just…” she starts before she curls her fingers just right, pressing them right against his prostate.

He moans, hips bucking up, his cock hardening completely. “Oh, fuck!” he cries out. “O-oh god, what— that’s my prostate?”

She laughs. “Yeah,” she nods as she keeps prodding at it, making a little bit of pre-come dribble right out of his cock. He digs his nails onto the mattress. “You’re perfect like this,” she says as she pulls her fingers out, putting the strap on around her waist, the harness a tad strange, but she makes do. She takes the lube once again and spurts a considerable amount on her hand before wrapping it around the dildo, stroking it and lubing it up properly. “Are you ready?”

He sucks in a breath. “I think so.” 

“It’s kind of taking your virginity, isn’t it?” she asks as she presses the head of the dildo right against his entrance, humming, stalling a little. “I think I like it.”

“I like it too,” he replies. “Come on, Eleanor, just— fuck me already.”

She sticks his tongue out at him and slowly presses in, pushing the dildo and seeing how his entrance stretches around it. He lets out a moan, tilting his head back as he grinds up against it.

“Oh God, that’s so weird,” he breathes out shakily.

She pushes deeper in, wishing she could feel it as she does so, gritting her teeth as she sinks furhter inside him, until her hips are flush against his ass cheeks. “You’re so good,” she breathes, leaning a hand up to caress his cheek. “So good. Can I move?”

Chidi draws in a shaky breath, looks at her with a small smile. “Yeah. Please move.”

She obliges, pulling out and pushing back in. She remains gentle, to not overwhelm him, panting as she works the dildo in and out of his ass, digging her nails into his hips as she fucks him. 

“God,” Chidi breathes, tilting his head back, staying there, pliant and ready. “I love it, god, Eleanor…”

“Shh,” she breathes out as she fucks him. “You’re doing so good for me. Just relax.”

She reaches a hand out for his cock, stroking him with slow, deliberate motions, watching him become even more of a mess underneath her, panting heavily.

“Eleanor,” he breathes out, desperate, as she hits his prostate again and again, eyes rolling back a little. “Eleanor, please…”

“Shh,” she breathes, stroking him harder. “Come for me.”

He does, breathing hard as he releases all over her hand, climaxing as he moans loudl and whiny, wriggling and twitching underneath her.

“So good,” she breathes, pulling her hand away and cleaning it off on the bedsheets. She slowly pulls out of him, takes the harness off. “I’m dripping. Are you destroyed enough that I have to get myself off?”

“Of course not, who do you think I am?” he replies through gasps. “Just give me a minute.”

Eleanor laughs and leans in to kiss him. “I’ll give you all the minutes in eternity.”


End file.
